(Dimethyl sulfoxide-κO)[2-({(ethyl-sulfan-yl)[2-(2-oxidobenzyl-idene-κO)hydrazin-yl-idene-κN]meth-yl}-imino-meth-yl)-phenol-ato-κO]dioxidouranium(VI).

The U(VI) atom in the title complex, [U(C(17)H(15)N(3)O(2)S)O(2)(C(2)H(6)OS)], exists within a distorted penta-gonal-pyramidal geometry where the oxide atoms occupy axial positions [O-U-O = 177.84 (14)°] and the penta-gonal plane is defined by the N(2)O(2) atoms of the tetra-dentate Schiff base ligand and the O atom of the dimethyl sulfoxide mol-ecule. In the crystal, centrosymmetric aggregates are formed via pairs of C-H⋯O inter-actions. The azomethine C=N atoms and ethyl-thiolyl group are disordered over two orientations in a 0.828 (3):0.172 (3) ratio.

Related literature

For background to uranyl Schiff base complexes, see: Şahin et al. (2010 ▶); Özdemir et al. (2011 ▶).

Experimental

Crystal data

[U(C17H15N3O2S)O2(C2H6OS)]

M = 673.54

Monoclinic,

a = 11.6988 (3) Å

b = 15.4972 (3) Å

c = 12.2246 (3) Å

β = 105.714 (3)°

V = 2133.47 (9) Å3

Z = 4

Mo Kα radiation

μ = 7.84 mm−1

T = 100 K

0.18 × 0.12 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.333, T max = 0.508

19265 measured reflections

4927 independent reflections

4237 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.063

S = 1.01

4927 reflections

281 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.98 e Å−3

Δρmin = −1.52 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003789/hb6614sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003789/hb6614Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[U(C17H15N3O2S)O2(C2H6OS)]	F(000) = 1280
Mr = 673.54	Dx = 2.097 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8576 reflections
a = 11.6988 (3) Å	θ = 2.2–27.5°
b = 15.4972 (3) Å	µ = 7.84 mm−1
c = 12.2246 (3) Å	T = 100 K
β = 105.714 (3)°	Prism, red
V = 2133.47 (9) Å3	0.18 × 0.12 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	4927 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4237 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.044
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.5°
ω scan	h = −14→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −20→20
Tmin = 0.333, Tmax = 0.508	l = −15→11
19265 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0243P)2 + 4.2587P] where P = (Fo2 + 2Fc2)/3
4927 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.98 e Å−3
3 restraints	Δρmin = −1.52 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
U	0.364161 (13)	0.640410 (10)	0.689855 (13)	0.01292 (6)
S1	0.15547 (15)	0.46851 (11)	0.34195 (14)	0.0341 (5)	0.828 (3)
S1'	0.0795 (7)	0.3967 (5)	0.5070 (7)	0.034*	0.172 (3)
S2	0.58169 (11)	0.77489 (8)	0.88184 (11)	0.0260 (3)
O1	0.4057 (3)	0.72624 (19)	0.5554 (3)	0.0171 (7)
O2	0.3653 (3)	0.5871 (2)	0.8599 (3)	0.0257 (8)
O3	0.2236 (3)	0.69271 (19)	0.6677 (3)	0.0169 (7)
O4	0.5046 (2)	0.58833 (18)	0.7065 (3)	0.0168 (7)
O5	0.4562 (3)	0.7596 (2)	0.8050 (3)	0.0220 (7)
N1	0.3115 (3)	0.5629 (2)	0.4990 (3)	0.0145 (8)
N2	0.1805 (3)	0.4702 (2)	0.5585 (3)	0.0211 (9)	0.828 (3)
C8'	0.1805 (3)	0.4702 (2)	0.5585 (3)	0.0211 (9)	0.172
N3	0.2299 (3)	0.5040 (2)	0.6674 (3)	0.0150 (8)
C1	0.4713 (4)	0.7110 (3)	0.4855 (4)	0.0140 (9)
C2	0.5515 (4)	0.7744 (3)	0.4682 (4)	0.0194 (10)
H2	0.5603	0.8270	0.5096	0.023*
C3	0.6170 (4)	0.7605 (3)	0.3915 (4)	0.0204 (10)
H3	0.6708	0.8036	0.3812	0.025*
C4	0.6058 (4)	0.6841 (3)	0.3285 (4)	0.0195 (10)
H4	0.6517	0.6756	0.2761	0.023*
C5	0.5290 (4)	0.6222 (3)	0.3427 (4)	0.0194 (10)
H5	0.5202	0.5709	0.2986	0.023*
C6	0.4613 (4)	0.6331 (3)	0.4226 (4)	0.0157 (9)
C7	0.3764 (4)	0.5671 (3)	0.4269 (4)	0.0148 (9)
H7	0.3662	0.5222	0.3721	0.018*
N2'	0.2226 (4)	0.4984 (3)	0.4777 (4)	0.0225 (10)	0.172 (3)
C8	0.2226 (4)	0.4984 (3)	0.4777 (4)	0.0225 (10)	0.828 (3)
C9	0.0485 (5)	0.3874 (4)	0.3578 (6)	0.0248 (15)	0.828 (3)
H9A	0.0055	0.4093	0.4116	0.030*	0.828 (3)
H9B	−0.0105	0.3790	0.2834	0.030*	0.828 (3)
C9'	0.097 (3)	0.3909 (19)	0.3636 (16)	0.025*	0.172 (3)
H9'A	0.0164	0.3980	0.3113	0.030*	0.172 (3)
H9'B	0.1427	0.4426	0.3538	0.030*	0.172 (3)
C10	0.1023 (6)	0.3020 (5)	0.3993 (6)	0.0410 (18)	0.828 (3)
H10A	0.0395	0.2618	0.4051	0.061*	0.828 (3)
H10B	0.1588	0.3091	0.4742	0.061*	0.828 (3)
H10C	0.1437	0.2791	0.3458	0.061*	0.828 (3)
C10'	0.152 (3)	0.3162 (19)	0.320 (3)	0.041*	0.172 (3)
H10D	0.1517	0.3270	0.2410	0.061*	0.172 (3)
H10E	0.1065	0.2637	0.3240	0.061*	0.172 (3)
H10F	0.2339	0.3088	0.3665	0.061*	0.172 (3)
C11	0.1832 (4)	0.4694 (3)	0.7413 (4)	0.0167 (9)
H11	0.1265	0.4251	0.7142	0.020*
C12	0.2075 (4)	0.4904 (3)	0.8601 (4)	0.0183 (10)
C13	0.1371 (4)	0.4507 (3)	0.9225 (4)	0.0241 (11)
H13	0.0770	0.4111	0.8856	0.029*
C14	0.1538 (4)	0.4683 (4)	1.0362 (4)	0.0290 (12)
H14	0.1043	0.4424	1.0770	0.035*
C15	0.2443 (5)	0.5245 (3)	1.0904 (4)	0.0274 (11)
H15	0.2567	0.5363	1.1690	0.033*
C16	0.3160 (4)	0.5633 (3)	1.0326 (4)	0.0247 (11)
H16	0.3781	0.6004	1.0720	0.030*
C17	0.2984 (4)	0.5486 (3)	0.9154 (4)	0.0185 (10)
C18	0.6216 (5)	0.6806 (3)	0.9658 (4)	0.0290 (12)
H18A	0.5758	0.6778	1.0219	0.044*
H18B	0.7066	0.6824	1.0050	0.044*
H18C	0.6046	0.6296	0.9168	0.044*
C19	0.6776 (5)	0.7611 (5)	0.7925 (5)	0.0467 (16)
H19A	0.6667	0.8091	0.7384	0.070*
H19B	0.6589	0.7066	0.7508	0.070*
H19C	0.7603	0.7599	0.8390	0.070*

	U11	U22	U33	U12	U13	U23
U	0.01231 (9)	0.01200 (8)	0.01301 (9)	−0.00072 (6)	0.00096 (6)	−0.00015 (7)
S1	0.0401 (10)	0.0365 (9)	0.0277 (9)	−0.0149 (8)	0.0128 (8)	−0.0043 (8)
S2	0.0302 (7)	0.0166 (6)	0.0228 (6)	−0.0051 (5)	−0.0073 (5)	−0.0024 (5)
O1	0.0220 (16)	0.0111 (14)	0.0189 (16)	−0.0001 (12)	0.0067 (14)	0.0000 (13)
O2	0.0299 (18)	0.0282 (18)	0.0153 (16)	−0.0136 (15)	−0.0002 (15)	0.0032 (15)
O3	0.0139 (15)	0.0169 (15)	0.0200 (16)	0.0015 (13)	0.0043 (13)	0.0003 (14)
O4	0.0142 (15)	0.0110 (14)	0.0210 (16)	−0.0005 (12)	−0.0025 (13)	−0.0033 (13)
O5	0.0246 (17)	0.0159 (16)	0.0203 (17)	0.0008 (13)	−0.0027 (15)	−0.0029 (14)
N1	0.0130 (17)	0.0141 (18)	0.0143 (18)	−0.0002 (14)	0.0000 (15)	0.0009 (16)
N2	0.024 (2)	0.021 (2)	0.015 (2)	−0.0050 (17)	−0.0008 (18)	−0.0024 (18)
C8'	0.024 (2)	0.021 (2)	0.015 (2)	−0.0050 (17)	−0.0008 (18)	−0.0024 (18)
N3	0.0130 (17)	0.0159 (18)	0.0138 (18)	−0.0002 (15)	0.0001 (15)	0.0008 (16)
C1	0.0110 (19)	0.015 (2)	0.014 (2)	0.0033 (17)	−0.0005 (18)	0.0018 (18)
C2	0.024 (2)	0.014 (2)	0.020 (2)	−0.0011 (18)	0.006 (2)	0.0013 (19)
C3	0.021 (2)	0.015 (2)	0.026 (3)	−0.0033 (18)	0.008 (2)	0.005 (2)
C4	0.020 (2)	0.021 (2)	0.019 (2)	0.0057 (19)	0.010 (2)	0.004 (2)
C5	0.020 (2)	0.018 (2)	0.022 (2)	0.0042 (18)	0.010 (2)	0.003 (2)
C6	0.016 (2)	0.014 (2)	0.015 (2)	0.0026 (17)	0.0004 (18)	0.0012 (18)
C7	0.017 (2)	0.013 (2)	0.012 (2)	−0.0002 (17)	0.0006 (18)	−0.0017 (18)
N2'	0.021 (2)	0.018 (2)	0.022 (2)	−0.0031 (19)	−0.007 (2)	0.003 (2)
C8	0.021 (2)	0.018 (2)	0.022 (2)	−0.0031 (19)	−0.007 (2)	0.003 (2)
C9	0.013 (3)	0.026 (3)	0.033 (4)	−0.008 (3)	0.000 (3)	−0.005 (3)
C10	0.035 (4)	0.046 (4)	0.041 (4)	−0.009 (3)	0.008 (3)	−0.001 (4)
C11	0.012 (2)	0.015 (2)	0.020 (2)	−0.0007 (17)	−0.0003 (19)	0.0026 (19)
C12	0.017 (2)	0.019 (2)	0.017 (2)	0.0047 (18)	0.0018 (19)	0.004 (2)
C13	0.020 (2)	0.028 (3)	0.024 (3)	0.001 (2)	0.004 (2)	0.002 (2)
C14	0.025 (3)	0.041 (3)	0.024 (3)	0.001 (2)	0.012 (2)	0.009 (2)
C15	0.037 (3)	0.030 (3)	0.017 (2)	0.013 (2)	0.009 (2)	0.003 (2)
C16	0.033 (3)	0.021 (2)	0.015 (2)	0.001 (2)	−0.002 (2)	0.001 (2)
C17	0.024 (2)	0.012 (2)	0.017 (2)	0.0016 (18)	0.001 (2)	0.0013 (19)
C18	0.032 (3)	0.019 (2)	0.026 (3)	0.002 (2)	−0.009 (2)	0.000 (2)
C19	0.034 (3)	0.066 (4)	0.036 (3)	−0.020 (3)	0.004 (3)	−0.007 (3)

U—O1	2.267 (3)	C9—C10	1.494 (9)
U—O2	2.233 (3)	C9—H9A	0.9900
U—O3	1.787 (3)	C9—H9B	0.9900
U—O4	1.792 (3)	C9'—C10'	1.493 (13)
U—O5	2.395 (3)	C9'—H9'A	0.9900
U—N1	2.547 (4)	C9'—H9'B	0.9900
U—N3	2.603 (4)	C10—H10A	0.9800
S1—C9	1.821 (6)	C10—H10B	0.9800
S1'—C9'	1.819 (12)	C10—H10C	0.9800
S2—O5	1.532 (3)	C10'—H10D	0.9800
S2—C18	1.773 (5)	C10'—H10E	0.9800
S2—C19	1.779 (6)	C10'—H10F	0.9800
O1—C1	1.316 (5)	C11—C12	1.440 (6)
O2—C17	1.310 (6)	C11—H11	0.9500
N1—C7	1.312 (5)	C12—C13	1.407 (7)
N1—N2'	1.415 (5)	C12—C17	1.419 (6)
N2—N3	1.402 (5)	C13—C14	1.377 (7)
N3—C11	1.292 (6)	C13—H13	0.9500
C1—C2	1.414 (6)	C14—C15	1.393 (7)
C1—C6	1.419 (6)	C14—H14	0.9500
C2—C3	1.379 (6)	C15—C16	1.373 (7)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.398 (6)	C16—C17	1.409 (6)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.358 (6)	C18—H18A	0.9800
C4—H4	0.9500	C18—H18B	0.9800
C5—C6	1.425 (6)	C18—H18C	0.9800
C5—H5	0.9500	C19—H19A	0.9800
C6—C7	1.437 (6)	C19—H19B	0.9800
C7—H7	0.9500	C19—H19C	0.9800
O3—U—O4	177.84 (14)	S1—C9—H9A	108.7
O3—U—O2	94.71 (13)	C10—C9—H9B	108.7
O4—U—O2	87.36 (13)	S1—C9—H9B	108.7
O3—U—O1	89.60 (12)	H9A—C9—H9B	107.6
O4—U—O1	88.65 (12)	C10'—C9'—S1'	124 (2)
O2—U—O1	160.62 (11)	C10'—C9'—H9'A	106.4
O3—U—O5	89.31 (12)	S1'—C9'—H9'A	106.4
O4—U—O5	91.63 (12)	C10'—C9'—H9'B	106.4
O2—U—O5	81.36 (11)	S1'—C9'—H9'B	106.4
O1—U—O5	79.81 (11)	H9'A—C9'—H9'B	106.5
O3—U—N1	95.21 (13)	C9—C10—H10A	109.5
O4—U—N1	83.00 (12)	C9—C10—H10B	109.5
O2—U—N1	128.10 (12)	H10A—C10—H10B	109.5
O1—U—N1	70.05 (11)	C9—C10—H10C	109.5
O5—U—N1	149.45 (11)	H10A—C10—H10C	109.5
O3—U—N3	81.27 (12)	H10B—C10—H10C	109.5
O4—U—N3	98.90 (12)	C9'—C10'—H10D	109.5
O2—U—N3	69.45 (11)	C9'—C10'—H10E	109.5
O1—U—N3	129.92 (11)	H10D—C10'—H10E	109.5
O5—U—N3	148.30 (11)	C9'—C10'—H10F	109.5
N1—U—N3	62.04 (11)	H10D—C10'—H10F	109.5
O5—S2—C18	106.6 (2)	H10E—C10'—H10F	109.5
O5—S2—C19	105.3 (2)	N3—C11—C12	127.3 (4)
C18—S2—C19	98.3 (3)	N3—C11—H11	116.3
C1—O1—U	130.0 (3)	C12—C11—H11	116.3
C17—O2—U	142.8 (3)	C13—C12—C17	119.5 (4)
S2—O5—U	133.10 (18)	C13—C12—C11	117.6 (4)
C7—N1—N2'	116.1 (4)	C17—C12—C11	122.8 (4)
C7—N1—U	123.5 (3)	C14—C13—C12	121.2 (5)
N2'—N1—U	119.1 (3)	C14—C13—H13	119.4
C11—N3—N2	111.4 (4)	C12—C13—H13	119.4
C11—N3—U	128.4 (3)	C13—C14—C15	119.0 (5)
N2—N3—U	119.0 (3)	C13—C14—H14	120.5
O1—C1—C2	120.0 (4)	C15—C14—H14	120.5
O1—C1—C6	121.8 (4)	C16—C15—C14	121.4 (5)
C2—C1—C6	118.1 (4)	C16—C15—H15	119.3
C3—C2—C1	120.4 (4)	C14—C15—H15	119.3
C3—C2—H2	119.8	C15—C16—C17	120.8 (5)
C1—C2—H2	119.8	C15—C16—H16	119.6
C2—C3—C4	121.4 (4)	C17—C16—H16	119.6
C2—C3—H3	119.3	O2—C17—C16	120.7 (4)
C4—C3—H3	119.3	O2—C17—C12	121.2 (4)
C5—C4—C3	119.7 (4)	C16—C17—C12	118.1 (4)
C5—C4—H4	120.2	S2—C18—H18A	109.5
C3—C4—H4	120.2	S2—C18—H18B	109.5
C4—C5—C6	120.9 (4)	H18A—C18—H18B	109.5
C4—C5—H5	119.5	S2—C18—H18C	109.5
C6—C5—H5	119.5	H18A—C18—H18C	109.5
C5—C6—C1	119.5 (4)	H18B—C18—H18C	109.5
C5—C6—C7	117.3 (4)	S2—C19—H19A	109.5
C1—C6—C7	122.9 (4)	S2—C19—H19B	109.5
N1—C7—C6	126.2 (4)	H19A—C19—H19B	109.5
N1—C7—H7	116.9	S2—C19—H19C	109.5
C6—C7—H7	116.9	H19A—C19—H19C	109.5
C10—C9—S1	114.2 (4)	H19B—C19—H19C	109.5
C10—C9—H9A	108.7
O3—U—O1—C1	−149.9 (3)	O4—U—N3—N2	−89.6 (3)
O4—U—O1—C1	28.9 (3)	O2—U—N3—N2	−173.4 (3)
O2—U—O1—C1	107.0 (4)	O1—U—N3—N2	6.1 (3)
O5—U—O1—C1	120.8 (3)	O5—U—N3—N2	162.5 (3)
N1—U—O1—C1	−54.2 (3)	N1—U—N3—N2	−12.5 (3)
N3—U—O1—C1	−71.6 (4)	U—O1—C1—C2	−135.9 (3)
O3—U—O2—C17	43.8 (5)	U—O1—C1—C6	46.5 (5)
O4—U—O2—C17	−135.5 (5)	O1—C1—C2—C3	−177.2 (4)
O1—U—O2—C17	146.2 (4)	C6—C1—C2—C3	0.5 (6)
O5—U—O2—C17	132.4 (5)	C1—C2—C3—C4	0.4 (7)
N1—U—O2—C17	−56.6 (5)	C2—C3—C4—C5	0.1 (7)
N3—U—O2—C17	−35.0 (5)	C3—C4—C5—C6	−1.4 (7)
C18—S2—O5—U	−46.1 (3)	C4—C5—C6—C1	2.2 (7)
C19—S2—O5—U	57.7 (3)	C4—C5—C6—C7	175.9 (4)
O3—U—O5—S2	170.9 (3)	O1—C1—C6—C5	175.9 (4)
O4—U—O5—S2	−11.0 (3)	C2—C1—C6—C5	−1.7 (6)
O2—U—O5—S2	76.1 (3)	O1—C1—C6—C7	2.6 (6)
O1—U—O5—S2	−99.3 (3)	C2—C1—C6—C7	−175.1 (4)
N1—U—O5—S2	−90.0 (3)	N2'—N1—C7—C6	171.9 (4)
N3—U—O5—S2	98.9 (3)	U—N1—C7—C6	−21.1 (6)
O3—U—N1—C7	127.2 (3)	C5—C6—C7—N1	175.5 (4)
O4—U—N1—C7	−51.6 (3)	C1—C6—C7—N1	−11.0 (7)
O2—U—N1—C7	−132.7 (3)	N2—N3—C11—C12	−177.0 (4)
O1—U—N1—C7	39.5 (3)	U—N3—C11—C12	−9.7 (6)
O5—U—N1—C7	29.7 (4)	N3—C11—C12—C13	173.4 (4)
N3—U—N1—C7	−155.6 (4)	N3—C11—C12—C17	−6.6 (7)
O3—U—N1—N2'	−66.2 (3)	C17—C12—C13—C14	0.9 (7)
O4—U—N1—N2'	115.1 (3)	C11—C12—C13—C14	−179.2 (4)
O2—U—N1—N2'	34.0 (3)	C12—C13—C14—C15	−1.8 (7)
O1—U—N1—N2'	−153.8 (3)	C13—C14—C15—C16	0.7 (8)
O5—U—N1—N2'	−163.7 (3)	C14—C15—C16—C17	1.3 (7)
N3—U—N1—N2'	11.1 (3)	U—O2—C17—C16	−148.3 (4)
O3—U—N3—C11	−78.3 (4)	U—O2—C17—C12	32.4 (7)
O4—U—N3—C11	103.9 (4)	C15—C16—C17—O2	178.5 (4)
O2—U—N3—C11	20.1 (3)	C15—C16—C17—C12	−2.2 (7)
O1—U—N3—C11	−160.4 (3)	C13—C12—C17—O2	−179.6 (4)
O5—U—N3—C11	−4.1 (5)	C11—C12—C17—O2	0.4 (7)
N1—U—N3—C11	−179.0 (4)	C13—C12—C17—C16	1.1 (6)
O3—U—N3—N2	88.2 (3)	C11—C12—C17—C16	−178.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4i	0.95	2.48	3.322 (5)	147

Table 1

Selected bond lengths (Å)

U—O1	2.267 (3)
U—O2	2.233 (3)
U—O3	1.787 (3)
U—O4	1.792 (3)
U—O5	2.395 (3)
U—N1	2.547 (4)
U—N3	2.603 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4i	0.95	2.48	3.322 (5)	147

Symmetry code: (i) .